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Journal of Industrial and Environmental Chemistry
|
Volume 2
GREEN CHEMISTRY &
TECHNOLOGY
7
th
International Conference on
J u n e 1 8 - 2 0 , 2 0 1 8 | D u b l i n , I r e l a n d
Tom Brunzel et al., J Ind Environ Chem 2018, Volume 2 | DOI: 10.4066/2591-7331-C1-002
SELECTIVE WACKER OXIDATION
OF A MACROCYCLIC DIENE TO A
MONOUNSATURATED CARBONYL
COMPOUND USED FOR THE
FRAGRANCE INDUSTRY IN ONE STEP
Tom Brunzel
1
, Angela Köckritz
1
and
Johannes
Heppekhausen
2
1
Leibniz Institute for Catalysis, Germany
2
Symrise AG, Germany
K
etones are ubiquitous in nature and play an important role as synthetic
intermediates in organic synthesis and for the manufacture of bulk
chemicals. While the palladium-catalyzed oxidation of terminal olefins to
their corresponding methyl ketones, known as the Wacker oxidation, can
be achieved efficiently in just one step, the oxidation of internal olefins is
still challenging not least of its lower selectivity and reactivity. Multi-step
synthesis and drastic reaction conditions have been used conventionally
to overcome the lack of an efficient transformation of ketones from
internal olefins. Regarding the increasing demand for greener and
efficient processes, simplified methods are highly desirable. The Wacker
oxidation was investigated to produce a monounsaturated ketone from
a macrocyclic diene for a compound used in the fragrance industry. The
most challenging step besides overcoming the low reactivity of internal
olefin oxidation is to prevent substrate isomerization and formation of the
diketone. Thus, the aim of the study was to find a catalytic system which
could increase the conversion of the starting material and provide the
desired monoketone with high selectivity. Different systems facing the
aspects of green chemistry were investigated. Furthermore, parameters
such as reaction temperature, time, concentration of catalyst precursors
and co-catalyst/oxidant, solvent system, etc. were optimized. Especially
in situ formed cationic PdII-salts introduced by Grubbs et al. have
shown promising results. More detailed information will be given at the
conference.
Figure. Wacker oxidation of cyclohexadecadiene
to cyclohexadec-8-enone.
Tom Brunzel is a PhD student at the Universi-
ty of Rostock, Germany. As a member of the
department for heterogeneous catalytic pro-
cesses at the associated Leibniz Institute for
Catalysis, he focuses his work on selective
liquid phase oxidation reactions. His research
interests center around process optimization
in laboratory scale, reactor techniques and tran-
sition metal catalyzed oxidation reactions of
macrocyclic olefins. Tom Brunzel received his
undergraduate degree in chemistry at the Uni-
versity of Rostock, where he focused on organic
chemistry. He then moved to the Leibniz Insti-
tute for Catalysis where he got in touch with the
synthesis of flavors and fragrances for the first
time. Currently, he is still working on the devel-
opment and synthesis of fragrance molecules
for the fragrance industry.
tom.brunzel@catalysis.deBIOGRAPHY
O
Wacker oxidation